Paquin, J.-F. : 2024 Science of Synthesis, 2024/4: Modern Strategies in Organofluorine Chemistry 1 DOI: 10.1055/sos-SD-243-00001
Modern Strategies in Organofluorine Chemistry 1

1.2 Deoxyfluorination of Aliphatic Alcohols

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Buch

Herausgeber: Paquin, J.-F.

Autoren: Arimitsu, S. ; Barata-Vallejo, S. ; Brioche, J. ; Cahard, D. ; Charette, A. B. ; Chen, P. ; Crousse, B. ; De Borggraeve, W. M. ; Hu, M. ; Ismalaj, E. ; Joosten, A. ; Kordnezhadian, R. ; Lai, J. ; Liu, G. ; Luo, Y.-C. ; Peyrical, L. C. ; Postigo, A. ; Sammis, G. M. ; Shao, X. ; Shen, Q. ; Song, H.; Thomson, B. J. ; Wu, S.; Xu, C. ; Yerien, D. E. ; Zhang, X.

Titel: Modern Strategies in Organofluorine Chemistry 1

Online ISBN: 9783132458253; Buch-DOI: 10.1055/b000000921

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

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Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Typ: Mehrbändiges Werk


Abstract

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The selective incorporation of fluoroalkyl motifs into complex organic molecules represents a significant challenge in fluorine chemistry. Among the various methods allowing the synthesis of alkyl fluorides, the deoxyfluorination of aliphatic alcohols remains one of the most practical, especially because substrates are readily available. This transformation has been popularized by the use of diethylaminosulfur trifluoride (DAST) and N,N-bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) reagents. However, the safety and chemoselectivity issues related to these reagents have led to the development of innovative reagents and protocols to perform this key reaction. This review aims to highlight the recent progress made in the field of deoxyfluorination of aliphatic alcohols and to provide the reader with useful guidelines with a view to performing such a transformation.